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CHEM 331
1. [4 pts] Mevacor is used clinically to lower serum cholesterol levels. How many chiral centers does
Mevacor have? Circle the chiral carbons.
O
HO *
* * * *
Mevacor
8 Chiral Carbons
2. [4 pts] Draw a Fischer Projection for the following chiral, tetrahedral carbon:
Br
OH
CH2CH3
OH
H
Br
One possibility....
CH2CH3
CH3
HO
CH2CH3
(b)
CH2CH2Br
HOH2C
H
Br
4. [6 pts] A solution of an unknown compound X (3.0 g of X per 20 mL), when placed in a polarimeter
tube 2.0 dm long, was found to have an observed rotation of 1.8 . What is the specific rotation of X?
.
[]D = /(C )(l) = (-1.8)/ (0.15 g/mL)(2.0 dm) = -6
Dont forget Concentration is g/mL and the cell path length is in decimeters (1 dm = 10 cm)
5. [16 pts] Shown below are five compounds whose molecular formula is C6H12. Base the answers
to the questions below on these five structures.
a. List two isomers that would be constitutional isomers of each other C or E and any other on the list
b. List two isomers that would be diastereomers of each other D and either A or B
c. List two isomers that would be meso compounds. D and E have a plane of symmetry
d. Isomer A has an optical rotation of +35. What is the optical rotation of isomer B? -35
e. What is the optical rotation of isomer D? D is a diastereomer of A cant tell is optical rotation
6. [10 pts] Two stereoisomers are obtained from the reaction of HBr with (3S, 4S)-4-bromo-3-methyl1-pentene.
a. [4 pts] Draw the structures of the two stereoisomers that form, showing stereochemistry of the new
chiral center.
Br
Br
Br
Br
Br
HBr
Enantiomers
Diastereomers
Meso compounds
c. [4 pts] One of the stereoisomers is not optically active. Circle the optically inactive compound and
explain why it is optically inactive.
The circled compound is a meso compound contains a plane of symmetry thus its not optically
active
7. [21 pts] Draw the structure of the expected product(s) or reagent for each of the following
reactions, as required. Indicate the stereochemistry of the products where appropriate.
(a)
Cl
2 equiv. HCl
(b)
Cl
Br
1 equiv. Br2
Br
(c)
1. disiamylborane
2. NaOH, H2O2
H
O
(d)
O
1. O3
2. Zn, H3O+
OH
(e)
H2, Pd/CaCO3, Pb or
Na or Li, NH3
(f)
(g)
H2, Pd/C
HO
8. [16 pts] Synthesis: Devise a short sequence of reactions for the construction of the following
products. Write the required reagents on each arrow and draw the intermediate product(s) that
will form in your sequence to receive full credit.
a. [6 pts]
H2O, H2SO4,
HgSO4
1. NaNH, NH3
H
2. 1-Bromobutane
b. [10 pts]
1. NaNH2,
NH3
1. NaNH2,
NH3
2.
2.
Br
Br
H2, Pd/C
Cl
6-chloro-3-ethyl-5-isopropyl-1-nonen-8-yne